NOT LONG AGO, the conventional wisdom when it came to choosing an evening bag was: Find something understated and elegant that wouldn’t overshadow your much-agonized-over dress. Recently, however, that sober logic has been turned on its head by a rambunctious group of attention-seeking clutches that play with words—whether it’s a phrase, your own nickname or a jokey hashtag.

It’s easy to see the bags’ initial appeal. They’re undeniably fun, and if ever an accessory trend was tailor-made for social media, this is it. “You know you’re going to get 100 more ‘likes’ holding a bag like this in a picture,” said Justin O’Shea, buying director at online retailer Mytheresa. They’re conversation pieces in real life, too. “Everyone wants to talk to you about your bag, whether it’s the bartender or your dinner partner,” said Brett Heyman, founder of Edie Parker, whose pearlescent acrylic minaudières can be personalized or come with words like “Taken” and “Hello” on them.

Still, the bags can sometimes appear obnoxiously hammy—and all that fun doesn’t come cheap. Most top $1,000. “As a heterosexual man, there’s only so much quirkiness I can take before I say ‘It’s not funny anymore,’ ” added Mytheresa’s Mr. O’Shea. “I start wondering if a ‘YES’ on a bag is worth 1200 euros.”

The trick: Find a loquacious clutch with beauty and quirk. “There’s a fine line,” said Charlotte Olympia designer Charlotte Dellal, who offers novelty evening bags. “The message can be tongue in cheek, but the bag itself still has to look pretty on your dressing table.”